1,1,2,3,3,3-hexafluoroprop-1-ene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Hexafluoropropene (13 g, 0.086 mol) was added over 30 minutes to a stirred mixture of CH2═CH(CO)NHC(CH3)2CH2OH (5.0 g, 0.035 mol), acetonitrile (190 mL) and Cs2CO3 (1.0 g, 0.003 mol) at 15-20° C. The resultant light yellow solution was stirred for an additional 1 h, after which TLC analysis (eluting with CH2Cl2 and CH3OH; 17:1 v/v) indicated the reaction was complete. The solution was filtered, and the filtrate concentrated under reduced pressure to give CH2═CHC(O)NHC(CH3)2CH2OCF2CFHCF3 as a light brown liquid (7.5 g ). 19F NMR (CDCl3): δ−75.8 (m, 3F), −79.9 (dm, 1F), −82.8 (dm, 1F), and −212.3 (dm, 1F) ppm; 1H NMR (CDCl3): δ 6.2 (dd, 1H), 6.1 (dd, 1H), 5.6 (dd, 1H), 5.6 (brs, 1H, overlaps), 4.8 (dm, 2H, JHF=44 Hz), 4.2 (dm, 2H), 1.4 (s, 6H) ppm. after which TLC analysis (eluting with CH2Cl2 and CH3OH; 17:1 v/v) The solution was filtered the filtrate concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Hexafluoropropene (15 g, 0.10 mol) was added over 30 minutes (nitrogen atmosphere) at 0° C. to a stirred mixture of CH2═CH(CO)NHCH2CH2OH (6.25 g, 0.054 mol), acetonitrile (180 mL) and powdered K2CO3 (3.5 g). After complete addition, the stirred reaction mixture was gradually brought to room temperature (˜1 h). The resultant pale yellow solution was filtered, and the filtrate was concentrated at the rotary evaporator. The crude product was concentrated further at ˜2 mm Hg for 15 min on a vacuum line to afford 8.5 g of CH2═CH(CO)NHCH2CH2OCF2CFHCF3 as a light yellow, viscous liquid. EI/DIP MS: m/e 265 for M+ (C8H9F6NO); 19F NMR (CDCl3) δ−75.7 (m, 3F), −81.0 to −83.0 (ddm, 2 F), and −212.1 (m, 1 F) ppm. 1H NMR (CDCl3) δ 6.3 (dd, 1H), 6.2 (dd, 1H), 6.19 (dd, 1H), 5.7 (dd, 1H), 4.8 (dm, 1H, JHF=42 Hz), 4.1 (t, 2H) and 3.6 (dt, 2H). After complete addition the stirred reaction mixture was gradually brought to room temperature (˜1 h) The resultant pale yellow solution was filtered the filtrate was concentrated at the rotary evaporator The crude product was concentrated further at ˜2 mm Hg for 15 min on a vacuum line